There is something to be said about plans made in the spur of the moment. There is an immediacy to action, a feeling that you are finally taking life by the reigns and saying “Hey! I’m steering this horse!” But alongside this ecstatic notion is the dark unpinning of reality, that sometimes plans made without planning go terribly awry.

My best friend Pat and I are dumb. I’ve written about him on the blog before. He’s the one that accompanied me on our trip to Yellowstone, that misadventure that through some sort of life alchemy became and all around good experience. We have made it a habit to end up in unfortunate and mostly stupid situations, masterminded by our collective shortsightedness and dedication to bad jokes. Past misadventures have found us getting caught sneaking out of a sweet sixteen, being stuck together on a month long road trip, and Pat dragging me out of a pool when alcohol and my own body prevented me from being able to swim. With all of this in our past it would seem that a simple trip to visit a friend of ours in Connecticut could not be nearly as catastrophic. You would be so wrong in believing that.

First off, we didn’t tell our friend Rory that we were coming. We simply decided on a whim fanned by Pat’s girlfriend Kristen, that we would leave late on a Sunday night to go and see Rory before she left to go to London. So we drove the two hours around the Long Island Sound to Clinton, Connecticut. On the way we laughed and made jokes. Pointing out weird things like the WWE headquarters (which for some strange reason happens to be in Connecticut) or the Pearl Harbor Memorial Bridge (which while Pearl Harbor is a nice thing to commemorate, seems like a strange choice considering it opened in 2015 in a state more than four thousand miles from Pearl Harbor itself). Most of all we joked about what might happen if we drove all the way there and Rory wasn’t home. At the time it seemed like an impossible situation. She had to be home, we knew for a fact she was leaving the next day, but life has a funny way of kicking you in the teeth when you least expect it.

We pulled into Rory’s driveway at 10:00 PM. We turned off the car lights to make sure we didn’t wake up her family, and we called her. She didn’t pick up. Again, we tried calling her to no avail. The jovial nature we had on the ride there began to slowly dissolve, and slowly in its place crept in the fear and gravity of the situation we put ourselves in. You might be asking yourself now, why not just drive back? While it might seem like an easy and sensible solution to most people, we had already put in close to three hours in driving time into this joke, and we couldn’t just give up on the whole thing right there. Dedication to bad jokes is a tenet we pride ourselves on.

We began to weigh our options. We could sleep in the car. That’d be pretty funny, but with three people in the car it wouldn’t exactly be preferable. Ultimately we decided that it would be best to find a cheap motel to crash at and show up to Rory’s house early in the morning for a quick surprise visit and, no harm, no foul. Clinton is a touristy little town too, filled with tiny motels to crash at. Or so we thought anyways. The first motel we chose we immediately turned away from. The aura emanating from this place could only be matched by that of the Bates Motel from Hitchcock’s Psycho. Before that point we didn’t know that we had a bottom line for motels, but it turns out that the threat (or feeling of the threat) of being murdered in a small town in Connecticut was ours. The next place wasn’t much better, but by the time we found anything open it was beginning to approach 12:00 AM. I wish that I had pictures of it. The bed sheets were filled with cigarette burns, there were water marks on all the walls, the distinct smell of piss hung in the air like dense fog. We decided that the only way we could possibly make it through the night in this place would be through anesthetizing ourselves with copious amounts of alcohol.

Once again the three of us piled into the car, this time in search of something that would allow us to get through the night. An hour is spent racing from liquor store to liquor store (which are called packies in CT for a reason that I am still not able to discern) all of which are closed. After a woman working at a McDonald’s offers to help us track down some beer in a transaction that seems to be a little less than legal, it is revealed to us that all alcohol sales are illegal after 6:00 PM on Sundays. This is a shock to our collective New York system, where any 7-11 or bodega will sell you whatever you want, whenever you want it. It adds new context to the looks of the many convenience store workers we asked for beer that night, a look that at the time seemed confused and unaware but after which was actually a look of disgust at the blatant request for them to take part in an illicit transaction. Parked in the McDonald’s parking lot, lit only by the yellow fluorescence of the golden arches hung overhead, we decided that there was only one course of action left; we had to go back.

It’s amazing how the taste of defeat changes your view of the world. The funny signs seen from the road now seemed to be mocking us. As if the entire state of Connecticut was aware of our ignorance of their strange ways and was turning in on us in scornful laughter. We reached the town of Rye, New York after an hour and a half of driving. The first convenience store we found sold us beer, a six pack each, without batting an eye. I’m not afraid to admit that the scene brought me to small tears of elation. We made it back to our motel at around 4:00 AM. By 5:30 we had finished what we bought and after a few episodes of Forensic Files, the only show  on at that time of the morning, we were asleep. I awoke to my phone buzzing at 7:30, to find Rory outside our motel wondering why we were there and why we had left an absurd amount of voicemails on her phone. She took us, still slightly inebriated, to go get bagels and told us we had a lot of explaining to do.

– Tim Caston